6-(3-(2-fluorophenyl)propoxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde | 1355088-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(3-(2-fluorophenyl)propoxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde
• CAS: 1355088-70-8
• 化学式: C₂₁H₂₁FO₂
• 分子量: 324.395
• InChiKey: HGJIBRKSUNDITP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(3-(2-fluorophenyl)propoxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde 在 盐酸 、 sodium hydroxide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 1-({6-[3-(2-fluorophenyl)propoxy]-1-methyl-3,4-dihydro-2-naphthalenyl}methyl)-3-azetidinecarboxylic acid hydrochloride
  参考文献：
  名称：

  Structure–activity relationship studies of S1P agonists with a dihydronaphthalene scaffold

  摘要：

  Structure-activity relationship (SAR) of sphingosine-1-phosphate receptor agonists with a dihydronaphthalene scaffold was investigated. Compound 1 was modified to improve S1P(1) agonistic activity and in vivo peripheral lymphocyte lowering (PLL) activity without impairing selectivity over S1P(3) agonistic activity. A detailed SAR study of the terminal lipophilic part revealed that the introduction of substituents on the propylene linker and the terminal benzene ring influences in vitro and PLL activities. Compound 6n bearing a (S)-methyl group at the 2-position on the propylene linker and chlorine at the para-position on the terminal benzene ring showed potent hS1P(1) agonistic activity with excellent selectivity over hS1P(3) and in vivo PLL activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.048
• 作为产物：
  描述：

  3,4-二氢-6-(苯基甲氧基)-1(2H)-萘酮 在 盐酸 、 茴香硫醚 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 为溶剂， 生成 6-(3-(2-fluorophenyl)propoxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde
  参考文献：
  名称：

  Structure–activity relationship studies of S1P agonists with a dihydronaphthalene scaffold

  摘要：

  Structure-activity relationship (SAR) of sphingosine-1-phosphate receptor agonists with a dihydronaphthalene scaffold was investigated. Compound 1 was modified to improve S1P(1) agonistic activity and in vivo peripheral lymphocyte lowering (PLL) activity without impairing selectivity over S1P(3) agonistic activity. A detailed SAR study of the terminal lipophilic part revealed that the introduction of substituents on the propylene linker and the terminal benzene ring influences in vitro and PLL activities. Compound 6n bearing a (S)-methyl group at the 2-position on the propylene linker and chlorine at the para-position on the terminal benzene ring showed potent hS1P(1) agonistic activity with excellent selectivity over hS1P(3) and in vivo PLL activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.048